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Should the Trail Blazers Try to Get Ahead of a Damian Lillard Trade?

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The evolving Lillard situation is changing the landscape in Portland.

NBA: Portland Trail Blazers at Denver Nuggets Ron Chenoy-USA TODAY Sports

The Portland Trail Blazers have an interesting trade and free agency period ahead in the summer of 2021. They’ll need to make several decisions regarding their current roster, including how much they value nearly every member thereof.

In preparation for the big summer, Dave Deckard and Dia Miller of the Dave and Dia Podcast are asking each other — and you — whether to “Keep or Yeet” each member of the team.

The concept is pretty much like it sounds. Take one Blazers player. Do you keep him around for next season or show him the door?

Today we get to the biggest player on the roster—maybe in the history of Portland rosters—Damian Lillard. He is everything for this team. That would appear to make this the easiest “keep” ever. As it turns out...maybe not?

We hasten to point out that voting “Yeet” (colloquially: to toss away with authority, somewhat gleefully) does not mean that Dave and Dia dislike the player, think the player has no talent, or regret the player being a Blazer. There can be a thousand reasons to yeet your resident shooting guard, only some of which have to do with him.

Similarly, voting “Keep” does not indicate that Dave and Dia think the player is perfect, just that the reasons for keeping him outweigh the reasons for letting him go.

Dave: Ok, Dia. Big sigh. Deep breath. We’ve reached the end, the ultimate post. Here we go. Keep or Yeet...Damian Lillard.

Dia: This seems like possibly the easiest answer of all. To me, keeping Dame is on obvious, albeit somewhat selfish, choice. Dame is our star. We are really lucky to have him in Portland, and truthfully, he’s been taken for granted by the front office in my opinion. They have had years to fill a roster to support his prime, and here we are. So of course as a Blazer fan I want to keep Dame. As a Dame fan… it’s hard not to see why he might be better off somewhere else.

Dave: I understand the conundrum. I wish we didn’t have it. But this has been coming for a few years now, kind of like a final exam that it feels like the Blazers haven’t studied for. But since we’re here, I’m going to say something that I never in my life thought I would. The Blazers need to get value for Lillard while they can. The farther they get backed into a corner, the worse it’s going to be for everyone. They need to move him.

Everything is as good as it’s going to get on that front right now. He just came off of another incredible season. He had a memorable individual performance in the 2021 NBA Playoffs. He’s played 66 and 67 games over the last two years, which is lower than his 75-80 of the prior six, but he’s still seen as sound. If an injury were to force him down to 50 games or fewer, his durability will become an issue and his value would plummet. If he makes an overt trade demand his value will decrease too. If the Blazers are going to do it, now is the time.

Dia: I am not sure I will ever be at that point. I think this is what happens when you have a star as a franchise—-especially one that was drafted and came up in the franchise. There’s a sense in which you say, “We are going to eat the cost because he’s ours.” We let him play out until he retires or requests a trade, simply because he’s Damian Lillard and he’s ours. I can see both sides here but I don’t know if I can ever say I WANT him to go. Especially because that essentially means a re build, which isn’t as much fun as watching Dame in a a blazers jersey. so my official stance here is keep. I’ll add the asterisk that I wouldn’t fault him for wanting to move after everything that’s happened and the front office’s apparent lack of desire to build around him.

Dave: Want is a relative term. I don’t want him to go. But if he’s going to go, the Blazers need to get the maximum value possible for him, even if that requires them to be proactive about moving him.

Let’s get real. You can’t replace Lillard. There’s no trade or free agency avenue that will bring you that kind of transcendent superstar, at least not if you’re Portland. Nor can you hope that one of your current players will grow into that once-in-a-generation player. You have to draft that kind of player or hope you get them very early in their career, when their ability isn’t established yet.

If Dame leaves, the rest of this roster is high and dry. They can cling onto the playoffs for a season or two by their fingernails, but there’s no foreseeable path to contention in this generation that doesn’t center around Dame. Wholesale liquidation is the eventual outcome. If you can trade him now, at his peak value, and jump-start your future, that’s better than playing behind the eight ball six months or a year from now, looking to salvage the unsalvageable. You reset with draft picks and young players, let the rest of the roster expire naturally, and trade anyone with a long contract (read: CJ McCollum) at the deadline or next summer.

The only way around that scenario at this point is if you know Dame is staying. I’m willing to bet my whiskers that he’s not. And if we see that, the franchise does too,

Regrettably, for the reasons stated above, I’m voting to yeet Lillard. I wasn’t there when this series started. In fact many of the appraisals of other players have been predicated on Dame staying. But now that we get here, I’m facing this crushing reality: the Blazers don’t have a choice. They didn’t build around him adequately. They have to take control of the process before he does, even if that means letting him go.

Dia: I can’t. I can’t do it. I tried to be level headed and not let my emotions and randomness get in the way of this series (which I did, except for Carmelo Anthony, but really, who can be rational about him?). But this is where I draw the line. I can’t bring myself to do it. I want to keep Damian Lillard. I think we should keep him. I guess this is where you and I just don’t agree. We had a good run, Dave. We saw eye to eye on more than I thought we would. I definitely didn’t imagine Dame being one we didn’t agree on though!

Dave: Me neither. And dang the Blazers for making me get to this point, but I just don’t see a happy ending and I’m too much of a pragmatist to let it slide. I don’t think the Blazers have to move Lillard RIGHT now and they certainly shouldn’t fire-sale him. The whole point of getting back in control of the process was so they wouldn’t have to do that. But the wind has shifted and they’d better get up a sail pretty quickly, or else it’s likely to tip them over. My view will change the instant they pull off a deal to bring in a high-quality player next to Lillard. I pray for the day. But from what we know now, I’ve gotta say yeet.

How about you, Dear Readers? Can you stomach a yeet call on one of the best players in the history of the franchise or is it just too much? Let us know below, and thanks for playing along with Keep or Yeet!

CJ McCollum— Dave and Dia “yeet”

Norman Powell— Dave and Dia “keep”

Robert Covington— Dave and Dia “keep”

Jusuf Nurkic— Dave and Dia “yeet”

Derrick Jones, Jr.Dia “keep”, Dave “yeet”

Anfernee Simons— Dave and Dia “keep”

Carmelo Anthony Dia “keep”, Dave “yeet”

Nassir Little— Dia “keep”, Dave “keep with an asterisk”

CJ Elleby, Rondae Hollis-Jefferson, and Harry Giles III— Dia “keep, keep, keep”, Dave “yeet, yeet, yeet”.

Damian Lillard— Dia “keep”, Dave “yeet”